Synthesis of Neplanocin A and Its 3′-Epimer via an Intramolecular Baylis–Hillman Reaction

Tan, Yun Lei; Santhanakrishnan, Sridhar; Yang, Huihui; Chai, Christina L. L.; Tam, Eric

doi:10.1021/jo501248e

Cited by 18 publications

(14 citation statements)

References 83 publications

(41 reference statements)

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“…was added to a solution of 21 (2.94 g, 6.28 mmol, 1.0 eq.) HRMS (ESI-TOF) m/z: [MþH] þ Calculated for C 34 Compound 23 (0.524 g, 1.33 mmol, 1.0 eq.) 2-methoxypropene (5.80 mL, 62.8 mmol, 10.0 eq.)…”

Section: Tert-butyl (2r3r4r)-2-((benzyloxy)methyl)-4-(((tertbutyldimentioning

confidence: 99%

Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

2017

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a b s t r a c tAzanucleosides, sugar-modified nucleoside analogues containing a 4 0 nitrogen atom, have shown a lot of therapeutic potential, e.g. as anti-cancer and antiviral agents. We report the synthesis of a series of 2'homoazanucleosides, in which the nucleobase is attached to the 2'-position of the pyrrolidine ring via a methylene linker. A suitable orthogonally protected iminosugar was synthesized by ring closing metathesis and dihydroxylation as key steps and further converted to a series of 8 nucleoside analogues through Mitsunobu reaction with suitably protected nucleobases. The 5 0 position of the adenine analogue was then further derivatized with thiols to afford 2 additional compounds. The final compounds were evaluated for biological activity.

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Section: Tert-butyl (2r3r4r)-2-((benzyloxy)methyl)-4-(((tertbutyldimentioning

confidence: 99%

Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

2017

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“…Another analog of neplanocin, the (-)-3′-epi neplanocin A (22), was reported by Tan et al [8] through a reactional pathway conducive to the introduction of all desired stereocenters in one step ( Figure 4). The intermediate 20 was prepared in two steps, starting from the d -ribose in an overall yield of 60%.…”

Section: Synthesis Of the Carbocyclic Neplanocinsmentioning

confidence: 99%

“…Synthesis of 3′-epi neplanocin A.Data taken from[8] Synthesis of ara-neplanocin. Data taken from[10].…”

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confidence: 99%

Recent Progress for the Synthesis of Selected Carbocyclic Nucleosides

et al. 2015

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Nucleoside analogs are extremely useful for the development of therapeutic agents to control viral diseases and cancer. Among the numerous modifications on the nucleoside skeleton, replacement of the oxygen of the furanose ring by a CH2 group resulted in increased flexibility and higher resistance to phosphorylases and led to carbocyclic nucleoside analogs (or carbanucleosides). The broad spectrum of biological activities of carbocyclic nucleosides led to tremendous research interest in their syntheses. The article documents recent strategies for the synthesis of active carbocyclic nucleosides by presenting individual case studies, such as the neplanocins, entecavir and selected fluorinated carbocyclic nucleosides. Furthermore, it provides new insights into new directions for more potent and active carbocyclic nucleoside analogs.

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“…[5] Due to strong biological activities as well as interesting structural features, (amino)cyclopentitols attract attention of both biologists and organic chemists as potential therapeutics for the treatment of carbohydrate-metabolism-related disorders. Carbocyclic nucleosides such as neplanocin A (5), [13] aristeromycin (6) [14] and their numerous analogues [15][16][17][18][19] exhibit antiviral, antibacterial and antitumor activity. Carbocyclic nucleosides such as neplanocin A (5), [13] aristeromycin (6) [14] and their numerous analogues [15][16][17][18][19] exhibit antiviral, antibacterial and antitumor activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4a‐Carba‐d‐lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α‐Mannosidases

et al. 2019

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A synthetic approach to 4a‐carba‐d‐lyxofuranose derivatives starting from d‐lyxose is described. The protected 4a‐carba‐β‐d‐lyxofuranose was employed as the key intermediate for the synthesis of 4a‐carba‐d‐lyxofuranose derivatives including novel 1‐amino‐1‐deoxy‐4a‐carba‐d‐lyxofuranoses. Synthesized 4a‐carba‐d‐lyxofuranoses were evaluated as inhibitors of GH38 α‐mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α‐mannosidases from Drosophila melanogaster and commercial Jack bean α‐mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1‐amino‐1‐deoxy‐4a‐carba‐β‐d‐lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 µm). In addition, the results of biological evaluation were discussed by means of molecular modelling.

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Synthesis of Neplanocin A and Its 3′-Epimer via an Intramolecular Baylis–Hillman Reaction

Abstract: The key cyclopentenyl intermediate 11b was synthesized in 4 steps from d-ribose in 41% overall yield via an efficient intramolecular Baylis-Hillman reaction. This novel key intermediate can be modified easily and transformed to neplanocin A (1a) and its 3'-epimer (1b).

Cited by 18 publications

References 83 publications

Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

Efficient diastereoselective synthesis of a new class of azanucleosides: 2′-homoazanucleosides

Recent Progress for the Synthesis of Selected Carbocyclic Nucleosides

Synthesis of 4a‐Carba‐d‐lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α‐Mannosidases

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